I'm cutting in a bit late on this one but I do have to disagree with some of KellyRain's disposition on the masculine skirt.
"What makes a skirt feminine? 1. Cut and shape. 2. How tightly it fits. 3. Length. 4. Color can be important. 5. Type of pleats. 6. Type of slits or cuts.
I think a good masculine skirt is about a few things.
1. Fabric and texture: I think fine wool, rough wool, canvas, interesting cotton blends are all great. They range from casual to formal and can be made to look like working men's fabrics from the 1920s that has a rough finish and looks lived in. That makes for a great foundation."
I have skirts that are made from polyacetate and other similar materials making them floaty and twirly. Even having sequins on them. Polycotton is another material that it's difficult to get away from. There are members here that wear similar and still look like men.
"Problem is only high fashion makers are doing vintage type fabrics so far. But you can find women's kilts and skirts done in these fabrics if you look hard enough. Especially heavy cottons or linens for summer."
I can pick up skirts in heavy materials from mainline stores but prices put me off.
"2. Shape: I stay away from basic A frame, body con, tight pencil skirts and loose pleats because they tend to look feminine unless they are made of a manly fabric. Which is rare. I think shape really defines whether a skirt can look masculine or not. So I look for shapes that tie back to ancient and old men's skirts."
I keep away from anything straight and absolutely LOVE A-line which most of my skirts are. Bodycon can be difficult but I have some of those too.
There are skirters here that love pencil skirts and rock them but not for me. I like my stride unfettered.
"a. Kilt - No brainer
b. Long straight skirts, not too tight, not too A shape. Just a simple line. Not in a shiny fabric. Stretchy is ok but needs to have structure. Low slit for walking or a folded pleat to allow the skirt to stretch. No deep slits."
So now you're saying that A-line are ok just not too wide? Well I have skater skirts with a very wide hem and love them.
"c. Knee length pencil skirt. Not tight. Straight simple. Folds or 1-2 pleats instead of a slit so you can walk."
AFAIK most pencil skirts have slits, of necessity. Pencils with pleats, perhaps some of you pencillers can enlighten me on this?
"d. Over the knee pleated skirt or simple box skirts can be manly if they are the right material. This gets back to Greek, Roman and other old styles. Simple and manly. Not too high waist so they accent your manly waist."
Not too much to disagree with here.
"e. Long flowing. This is tricky. Has to be a skirt with heavy pleats, lots of very tight small pleats or slow widening at the bottom. Floor length. This gets back to ethnic designs from all over the world. But in an elegant fabric it will be very manly."
Carl may find difficulty with your thoughts. I have some ankle length broomstick type skirts that don't fall within your remit.
Grey, black, brown, more black, navy, dark earth tones. I avoid anything even vaguely pink or pastel, light colors (I just don't like them much) or colors that look very feminine. I tend to go for darker heavy colors in winter and simple summer neutral shades in summer."
Now I would have to blow you away. I LOVE bright colours and have skirts in black, bright blue and other shades, brown ( various shades ), green, purple, red, white, yellow among others. Nowt wrong with colour. In fact I shop on t'other side purely to get the bright colours, tops, bottoms, whatever.
"But it isn't just the skirt that makes an outfit manly or not. The upper is critical. I see young Japanese guys trying to wear the same uppers that girls do here and so they lose the masculine lines and look. My wife comments that some of the guys look like their Moms, though unintentionally.
To make an outfit masculine you need to care about the uppers. Your usual manly shirts are fine. Add a vintage vest, a shorter (not too short) length blazer that is the same color or a good matching color to the skirt. It looks masculine and it can be a very good way to assure it looks manly. "
I and many others on this site wear women's tops - cami's, blouses, T-shirts, jumpers. Some of my favourites are feminine. Of course I wear button up shirts as well.
"Shoes. Working man's boots. Trickers from the UK, Dr. Martins, Monkey Boots are look great with the shorter skirts. If you like taller boots Dr. Martins or logger boots are great. Especially in winter. For dressy long skirts or dressy kilts go with a nice dress shoe. Over the ankle is better. I avoid high heels or flats."
Creepers or monkey boots instantly make a skirt look manly.
Footwear has a few threads on this. Heels are ok, pumps, Mary Janes, why not? If you're going to wear a skirt and top, tights then why not the shoes?
I do have to admit that I still have this bridge to cross over.
Finally, your attitude.
Probably THE most important factor to getting around almost invisibly. Agreed.
So that's my take and my wardrobe reflects that. In the end, a man wearing a skirt will choose something that reflects attitude, character, taste and upbringing
I believe in offering every assistance short of actual help but then mainly just want to be left to be myself in all my difference and uniqueness.